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Solvent- or Temperature-Controlled Diastereoselective Aldol Reaction of Methyl Phenylacetate

P. Veeraraghavan Ramachandran* and Prem B. Chanda

*Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States, Email:

P. V. Ramachandran, P. B. Chanda, Org. Lett., 2012, 14, 4346-4349.

DOI: 10.1021/ol301782s


The choice of either the solvent or temperature determines the diastereoselectivity during the enolboration-aldolization of methyl phenylacetate. In CH2Cl2, the reaction favors the anti-pathway at -78 C and the syn-pathway at rt. Conversely, the reaction produces the anti-isomer up to rt and the syn-isomer at refluxing temperatures in nonpolar solvents.

see article for more examples

Temperature- and Reagent-Controlled Complementary Syn- and Anti-Selective Enolboration-Aldolization of Substituted Phenylacetates

A. Y. Thomas, T. L. Walls III, B. N. Nelson, S. W. Primeaux, P. B. Chanda, J. Org. Chem., 2021, 86, 6184-6194.

Key Words

β-hydroxy esters

ID: J54-Y2012-2790